反応 #1183249

反応方程式

acetaldehyde

(S)-4-amino-2-(tert-butoxycarbonylamino) butanoic acid

water MeOH

NaCNBH3

acetaldehyde

→

(S)-2-amino-4-(diethylamino)butanoic acid

反応条件

後処理

1. 1
   その他the cooling bath was removed
2. 2
   workup.STIRRINGthe reaction was stirred for 20.5 hr
3. 3
   その他Most of the MeOH component was removed in vacuo
4. 4
   workup.ADDITIONthe remaining mixture was treated with concentrated HCl until its pH
5. 5
   その他The volatile component was removed in vacuo
6. 6
   workup.ADDITIONthe residue was treated with 4 M HCl/dioxane (20 mL)
7. 7
   workup.STIRRINGstirred at ambient condition for 7.5 hr
8. 8
   その他The volatile component was removed in vacuo
9. 9
   その他the residue was purified with DOWEX® 50WX8-100 ion-exchange resin (column
10. 10
    洗浄was washed with water
11. 11
    洗浄the compound was eluted with dilute NH4OH
12. 12
    その他prepared from 18 ml of NH4OH and 282 ml of water)

実験手順

NaCNBH3 (1.60 g, 24.2 mmol) was added in batches to a chilled (˜15° C.) water/MeOH (12 mL each) solution of (S)-4-amino-2-(tert-butoxycarbonylamino) butanoic acid (2.17 g, 9.94 mmol). A few minutes later acetaldehyde (2.7 mL, 48.1 mmol) was added drop-wise over 2 min, the cooling bath was removed, and the reaction mixture was stirred at ambient condition for 3.5 hr. An additional acetaldehyde (2.7 mL, 48.1 mmol) was added and the reaction was stirred for 20.5 hr. Most of the MeOH component was removed in vacuo, and the remaining mixture was treated with concentrated HCl until its pH reached ˜1.0 and then heated for 2 hr at 40° C. The volatile component was removed in vacuo, and the residue was treated with 4 M HCl/dioxane (20 mL) and stirred at ambient condition for 7.5 hr. The volatile component was removed in vacuo and the residue was purified with DOWEX® 50WX8-100 ion-exchange resin (column was washed with water and the compound was eluted with dilute NH4OH, prepared from 18 ml of NH4OH and 282 ml of water) to afford intermediate (S)-2-amino-4-(diethylamino)butanoic acid as an off-white solid (1.73 g).

出典